Hydrogen Peroxide → (2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylbutanoic acid

HRID 32838

Reaction equation

HRID 32838 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([C:17](N1[C@@H](C2C=CC=CC=2)COC1=O)=[O:18])[C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].OO.[OH-].[Li+].S([O-])(O)=[O:37].[Na+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:7][C@@H:8]([C@@H:9]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:10])[C:17]([OH:18])=[O:37])=[O:31])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 3939Lithium HydroxideHCID 23665763Sodium BisulfiteHCID 69144778[(1S,2R)-1-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 2734507(2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylbutanoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(1S,2R)-1-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester (710 mg, 1.7 mmol) in tetrahydrofuran (18 mL) and water (4 ml) at 0° C. was added 30% aqueous hydrogen peroxide (1.5 mL, 15.1 mmol) followed by 1M aqueous lithium hydroxide (5.0 mL, 5.0 mmol). The mixture was stirred overnight at room temperature. The excess hydrogen peroxide was quenched with 2.0 M aqueous sodium hydrogen sulfite (15 mL, 30.1 mmol). Stirring was continued for 1 hour followed by extraction with dichloromethane. The aqueous layer was acidified with 10% aqueous citric acid and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water, brine and dried over magnesium sulfate and evaporated to give (2S,3R)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid (420 mg, 90% yield).

Workup

  1. stirringStirring
  2. waitwas continued for 1 hour
  3. extractionfollowed by extraction with dichloromethane
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-facdbf49ab0b4c3093e0e254217d244b
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Linked notes

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